3-Carbamoylquinoxalin-1-ium chloride.

The title compound, C(9)H(8)N(3)O(+)·Cl(-), was isolated from a liquid culture of streptomyces sp. In the cation, the ring system makes a dihedral angle of 0.2 (2)° with the amide group. The protonation creating the cation occurs at ome of the N atoms in the quinoxaline ring system. In the crystal, the ions are linked through N-H⋯O and N-H⋯Cl hydrogen bonds, forming a two-dimensional network parallel to (10[Formula: see text]).

Related literature

For a description of the bioactivity and mode of action of compounds containing the quinoxaline moiety, see: Bailly et al. (1999 ▶); May et al. (2004 ▶); Mollegaard et al. (2000 ▶); Waring (1993 ▶). For crystal structures of the mol­ecules triostin A, echinomycin and their derivatives, which all contain two quinoxalines, see: Hossain et al. (1982 ▶); Sheldrick et al. (1984 ▶, 1995 ▶); Viswamitra et al. (1981 ▶); Wang et al. (1984 ▶); Ughetto et al. (1985 ▶). For a description of the Streptomycete producing the title compound, see: Castillo et al. (2003 ▶).

Experimental

Crystal data

C9H8N3O+·Cl−

M = 209.63

Monoclinic,

a = 5.6476 (2) Å

b = 15.1045 (9) Å

c = 11.2556 (6) Å

β = 99.993 (3)°

V = 945.58 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.37 mm−1

T = 150 K

0.25 × 0.20 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997 ▶) T min = 0.913, T max = 0.971

3671 measured reflections

2147 independent reflections

1798 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.085

S = 1.05

2147 reflections

160 parameters

All H-atom parameters refined

Δρmax = 0.25 e Å−3

Δρmin = −0.24 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: WinGX (Farrugia, 1999 ▶) and ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811052457/lh5381sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811052457/lh5381Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811052457/lh5381Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C9H8N3O+·Cl−	F(000) = 432
Mr = 209.63	Dx = 1.473 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1998 reflections
a = 5.6476 (2) Å	θ = 1.0–27.5°
b = 15.1045 (9) Å	µ = 0.37 mm−1
c = 11.2556 (6) Å	T = 150 K
β = 99.993 (3)°	Plate, pale yellow
V = 945.58 (8) Å3	0.25 × 0.20 × 0.08 mm
Z = 4

Nonius KappaCCD diffractometer	2147 independent reflections
Radiation source: fine-focus sealed tube	1798 reflections with I > 2σ(I)
graphite	Rint = 0.018
φ and ω scans	θmax = 27.5°, θmin = 3.9°
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	h = −7→7
Tmin = 0.913, Tmax = 0.971	k = −18→19
3671 measured reflections	l = −14→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034	All H-atom parameters refined
wR(F2) = 0.085	w = 1/[σ2(Fo2) + (0.0397P)2 + 0.2499P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2147 reflections	Δρmax = 0.25 e Å−3
160 parameters	Δρmin = −0.24 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.012 (4)

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm that effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Cl1	0.08949 (6)	0.30272 (3)	0.19526 (3)	0.03255 (15)
O1	0.76925 (19)	0.43611 (7)	0.55896 (10)	0.0336 (3)
N1	0.4423 (2)	0.39023 (9)	0.42509 (12)	0.0269 (3)
N2	0.6771 (2)	0.23505 (8)	0.39555 (10)	0.0234 (3)
N3	1.1403 (2)	0.21019 (8)	0.51784 (11)	0.0248 (3)
C1	0.6625 (3)	0.38080 (9)	0.48828 (13)	0.0247 (3)
C2	0.7884 (2)	0.29539 (9)	0.46906 (12)	0.0234 (3)
C3	1.0240 (3)	0.28321 (10)	0.53318 (13)	0.0254 (3)
C4	1.0391 (2)	0.14589 (9)	0.43990 (12)	0.0237 (3)
C5	1.1680 (3)	0.06898 (10)	0.42012 (14)	0.0289 (3)
C6	1.0562 (3)	0.00651 (11)	0.34196 (14)	0.0338 (4)
C7	0.8153 (3)	0.01774 (11)	0.28407 (14)	0.0331 (4)
C8	0.6884 (3)	0.09223 (10)	0.30207 (13)	0.0276 (3)
C9	0.7997 (2)	0.15942 (9)	0.37975 (12)	0.0229 (3)
H1A	0.370 (3)	0.4397 (13)	0.4318 (16)	0.036 (5)*
H1B	0.381 (4)	0.3498 (15)	0.3699 (19)	0.051 (6)*
H3	1.102 (3)	0.3227 (12)	0.5857 (17)	0.035 (5)*
H3N	1.290 (3)	0.2011 (11)	0.5682 (17)	0.034 (5)*
H5	1.324 (3)	0.0634 (12)	0.4615 (16)	0.035 (5)*
H6	1.139 (3)	−0.0467 (12)	0.3273 (15)	0.032 (4)*
H7	0.738 (3)	−0.0276 (13)	0.2325 (17)	0.041 (5)*
H8	0.523 (3)	0.1023 (10)	0.2602 (15)	0.027 (4)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0270 (2)	0.0419 (2)	0.0258 (2)	−0.00693 (15)	−0.00344 (14)	−0.00243 (15)
O1	0.0323 (6)	0.0264 (5)	0.0365 (6)	0.0033 (4)	−0.0097 (5)	−0.0054 (5)
N1	0.0258 (6)	0.0235 (6)	0.0284 (7)	0.0029 (5)	−0.0037 (5)	−0.0018 (5)
N2	0.0240 (6)	0.0249 (6)	0.0205 (6)	−0.0011 (5)	0.0015 (5)	0.0019 (5)
N3	0.0217 (6)	0.0290 (6)	0.0225 (6)	0.0013 (5)	0.0000 (5)	0.0016 (5)
C1	0.0263 (7)	0.0231 (7)	0.0228 (7)	−0.0001 (6)	−0.0011 (5)	0.0023 (6)
C2	0.0235 (7)	0.0251 (7)	0.0212 (7)	−0.0014 (5)	0.0030 (5)	0.0016 (5)
C3	0.0244 (7)	0.0268 (7)	0.0232 (7)	−0.0009 (6)	−0.0007 (6)	−0.0007 (6)
C4	0.0253 (7)	0.0258 (7)	0.0204 (7)	−0.0011 (5)	0.0051 (5)	0.0029 (5)
C5	0.0286 (8)	0.0315 (8)	0.0274 (8)	0.0053 (6)	0.0075 (6)	0.0033 (6)
C6	0.0433 (9)	0.0288 (8)	0.0321 (8)	0.0056 (7)	0.0144 (7)	−0.0001 (7)
C7	0.0428 (9)	0.0303 (8)	0.0279 (8)	−0.0050 (7)	0.0102 (7)	−0.0071 (7)
C8	0.0296 (8)	0.0314 (8)	0.0220 (7)	−0.0046 (6)	0.0052 (6)	−0.0018 (6)
C9	0.0257 (7)	0.0246 (7)	0.0189 (7)	−0.0008 (6)	0.0050 (5)	0.0022 (5)

O1—C1	1.2361 (17)	C3—H3	0.900 (19)
N1—C1	1.3285 (18)	C4—C5	1.409 (2)
N1—H1A	0.86 (2)	C4—C9	1.4178 (19)
N1—H1B	0.90 (2)	C5—C6	1.368 (2)
N2—C2	1.3154 (18)	C5—H5	0.928 (17)
N2—C9	1.3635 (18)	C6—C7	1.413 (2)
N3—C3	1.3104 (19)	C6—H6	0.957 (18)
N3—C4	1.3660 (19)	C7—C8	1.368 (2)
N3—H3N	0.94 (2)	C7—H7	0.95 (2)
C1—C2	1.5066 (19)	C8—C9	1.414 (2)
C2—C3	1.411 (2)	C8—H8	0.980 (16)
C1—N1—H1A	117.3 (12)	N3—C4—C9	117.53 (13)
C1—N1—H1B	120.9 (13)	C5—C4—C9	121.29 (13)
H1A—N1—H1B	121.2 (18)	C6—C5—C4	118.49 (15)
C2—N2—C9	117.67 (12)	C6—C5—H5	123.5 (11)
C3—N3—C4	121.30 (13)	C4—C5—H5	118.0 (11)
C3—N3—H3N	117.5 (10)	C5—C6—C7	120.93 (15)
C4—N3—H3N	120.9 (10)	C5—C6—H6	120.4 (10)
O1—C1—N1	125.36 (13)	C7—C6—H6	118.6 (10)
O1—C1—C2	118.78 (12)	C8—C7—C6	121.19 (15)
N1—C1—C2	115.85 (12)	C8—C7—H7	118.8 (11)
N2—C2—C3	122.45 (13)	C6—C7—H7	120.0 (11)
N2—C2—C1	119.85 (12)	C7—C8—C9	119.58 (14)
C3—C2—C1	117.69 (12)	C7—C8—H8	122.4 (9)
N3—C3—C2	119.48 (13)	C9—C8—H8	118.0 (9)
N3—C3—H3	116.4 (12)	N2—C9—C8	120.04 (13)
C2—C3—H3	124.2 (12)	N2—C9—C4	121.50 (13)
N3—C4—C5	121.17 (13)	C8—C9—C4	118.46 (13)
C9—N2—C2—C3	−1.7 (2)	C9—C4—C5—C6	−0.6 (2)
C9—N2—C2—C1	179.05 (12)	C4—C5—C6—C7	−1.3 (2)
O1—C1—C2—N2	179.06 (13)	C5—C6—C7—C8	1.6 (2)
N1—C1—C2—N2	−1.63 (19)	C6—C7—C8—C9	0.1 (2)
O1—C1—C2—C3	−0.2 (2)	C2—N2—C9—C8	179.78 (13)
N1—C1—C2—C3	179.12 (13)	C2—N2—C9—C4	−0.14 (19)
C4—N3—C3—C2	0.7 (2)	C7—C8—C9—N2	178.09 (13)
N2—C2—C3—N3	1.5 (2)	C7—C8—C9—C4	−2.0 (2)
C1—C2—C3—N3	−179.26 (12)	N3—C4—C9—N2	2.22 (19)
C3—N3—C4—C5	177.53 (13)	C5—C4—C9—N2	−177.80 (12)
C3—N3—C4—C9	−2.5 (2)	N3—C4—C9—C8	−177.70 (12)
N3—C4—C5—C6	179.33 (13)	C5—C4—C9—C8	2.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.86 (2)	2.04 (2)	2.9008 (17)	173.5 (17)
N1—H1B···Cl1	0.90 (2)	2.44 (2)	3.2590 (13)	152.0 (17)
N3—H3N···Cl1ii	0.94 (2)	2.02 (2)	2.9501 (13)	169.8 (15)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.86 (2)	2.04 (2)	2.9008 (17)	173.5 (17)
N1—H1B⋯Cl1	0.90 (2)	2.44 (2)	3.2590 (13)	152.0 (17)
N3—H3N⋯Cl1ii	0.94 (2)	2.02 (2)	2.9501 (13)	169.8 (15)

Symmetry codes: (i) ; (ii) .